Rudebusch, Gabriel
Fix, Aaron
Henthorn, Hilary
Vonnegut, Chris
Zakharov, Lev
Haley, Michael
2014-09-11T21:54:05Z
2014-09-11T21:54:05Z
2014-06-16
http://dx.doi.org/10.1039/C4SC01432D
1. Rudebusch GE, Fix AG, Henthorn HA, Vonnegut CL, Zakharov LN, Haley MM. Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials. Chem Sci. 2014;5(9):3627. doi:10.1039/C4SC01432D.
2041-6539
http://hdl.handle.net/1794/18239
We report the preparation and characterization of a new class of quinoidal thienoacenes. The synthetic route is efficient, high-yielding and scalable with the potential for further functionalization. Single crystal X-ray diffraction reveals that, as size increases, the molecules pack in progressively closer 1D arrangements. The title compounds are shown to have amphoteric redox behaviour by cyclic voltammetry. The anion radicals are studied by EPR spectrometry and by computations. The electron-accepting nature, NIR absorption and the low-lying LUMO energies (ca. −4.0 eV) allude to potential use in materials applications.
We thank the National Science Foundation (CHE-1301485) for support of this research as well as support in the form of instrumentation (CHE-0840478 and CHE-0923589) and computer grants (OCI-0960354). We also thank Dr Brad Rose for guidance on the EPR and computational studies and Prof. Mark Lonergan (University of Oregon) for use of his group's potentiostat. HRMS were obtained at the Mass Spectrometry Facilities and Services Core of the Environmental Health Sciences Center, Oregon State University, supported by grant #P30-ES00210, National Institute of Environmental Health Sciences, National Institutes of Health.
en_US
Royal Society of Chemistry
Creative Commons BY-NC-SA
quinoidal thienoacenes
chemical synthesis
organic electronics
Quinoidal diindenothienoacenes: synthesis and properties of new functional organic materials
Article

Young, Brian
Chase, Daniel
Marshall, Jonathan
Vonnegut, Chris
Zakharov, Lev
Haley, Michael
2014-09-11T22:20:04Z
2014-09-11T22:20:04Z
2013-12-10
http://dx.doi.org/10.1039/C3SC53181C
Young BS, Chase DT, Marshall JL, Vonnegut CL, Zakharov LN, Haley MM. Synthesis and Properties of Fully-Conjugated Indacenedithiophenes. Chem Sci. 2014;5(3):1008–1014. doi:10.1039/C3SC53181C.
2041-6539
http://hdl.handle.net/1794/18240
The synthesis and characterization of four fully-conjugated indacenedithiophenes (IDTs) are disclosed. In contrast to anthradithiophenes, regioselective synthesis of both syn and anti isomers is readily achieved. Thiophene fusion imparts increased paratropic character on the central indacene core as predicted by DFT calculations and confirmed by 1H NMR spectroscopy. IDTs exhibit red-shifted absorbance maxima with respect to their all-carbon analogues and undergo two-electron reduction and one-electron oxidation.
We thank the National Science Foundation (CHE-1013032 and CHE-1301485) for support of this research as well as support in the form of instrumentation (CHE-0923589) and computer grants (OCI-0960354). We also thank Prof. Mark Lonergan (University of Oregon) for use of his group's potentiostat. HRMS were obtained at the Mass Spectrometry Facilities and Services Core of the Environmental Health Sciences Center, Oregon State University, supported by grant #P30-ES00210, National Institute of Environmental Health Sciences, National Institutes of Health.
en_US
Chemical Science
Creative Commons BY-NC-SA
indacenedithiophenes
paratropic character
chemical synthesis
organic electronics
Synthesis and properties of fully-conjugated indacenedithiophenes
Article